Phenylacetyl isothiocyanate → HCID 24983281, compound

HRID 1676251Notes

Reaction equation

HRID 1676251 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([CH2:18][CH2:19][CH3:20])[S:17][C:10]=12.[C:22]1([CH2:28][C:29]([N:31]=[C:32]=[S:33])=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:21][C:32]([NH:31][C:29](=[O:30])[CH2:28][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[S:33])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([CH2:18][CH2:19][CH3:20])[S:17][C:10]=12

Participants

4

Reactant 2

HCID 12454157Phenylacetyl isothiocyanateHCID 67348795HCID 67348795, compound

Product 1

HCID 24983281HCID 24983281, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 3-fluoro-4-(2-propylthieno[3,2-b]pyridin-7-yloxy)benzenamine (8 mg, 0.03 mmol) and 2-phenylethanoyl isothiocyanate (9 mg, 0.05 mmol; prepared according to J. Org. Chem. 1964, 29, 1115-1119) in 1:1 toluene/ethanol (0.5 mL) were stirred at room temperature for 2 hours. The reaction mixture was purified by preparative TLC (5% MeOH/EtOAc). The product was obtained as a waxy solid (8 mg, 58%). 1H NMR (400 MHz, CDCl3) δ 12.49 (s, 1H), 8.57 (s, 1H), 8.45 (m, 1H), 7.94 (m, 1H), 7.44 (m, 4H), 7.32 (m, 2H), 7.25 (m, 2H, overlaps chloroform), 6.48 (m, 1H), 3.76 (s, 2H), 2.93 (m, 2H), 1.81 (m, 2H), 1.04 (m, 3H). LRMS (ESI neg) m/e 478 (M−1).

Workup

  1. customThe reaction mixture was purified by preparative TLC (5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-fad573f56f83456abd4cd44da37ba9d8
Source dataset
uspto-grants-2011_08
Patent number
US08003662B2

Reaction notes

Loading…